Tetrahedron

The fischer indole synthesis of 8-methyl-5-substituted-1-oxo-β-carbolines: A remarkable high yield of a [1, 2]-methyl migration.

SV Luis, MI Burguete

Index: Luis,S.V.; Burguete,M.I. Tetrahedron, 1991 , vol. 47, p. 1737

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Citation Number: 12

Abstract

A very unusual high yield of rearranged products (via methyl migration) has been obtained in the Fischer indole cyclization of the 3-(2, 5-dimethyl phenylhydrazone) of 2, 3-piperidine dione (6b). When a less activated aromatic ring is present in the phenylhydrazone 6, such a behaviour is not observed and cyclization occurs essentially without rearrangement.